Sensitizing of silver halide emulsions



FIPRIM 0R 2,312,153 SGZifCh Room SENSITIZING OF SILVER HALIDE EHULSIONS Filed May 7, 1940 F1 1 Unsensrtizzd Sflver CHoride Emulsion F1 2 silvrcwondazmumon swim with thzDya of ExamplaH Fig.3 SiMrCHoridaEmulsion sensitized wlth thQDyQ Of' Eiampbm Mia/we?- .Detcrle I mvmoa IS ATTORNEYS Patented Feb. 23, 1943 UNITED STATES Search Room PATENT OFFICE SENSITIZING OF SILVER HALIDE EMULS IONS Walter Dieterle, Dessau-Ziebigk, Germany, as-

signor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware Application May 7, 1940, Serial No. 333,761 In Germany May 15, 1939 4Claims.

together with sensitizers of other groups. The manufacture of the dyestufls is accomplished according to U. S. Patent No. 2,155,459.

The invention is illustrated by the accompany- 5 ing self-explanatory drawing, depicting the sensitivities of silver halide emulsions sensitized with the dyes of Examples Ii and III, especially when taken with the following examples.

Example I sensitizing maximum at 505 mu.

Example II S -CH,

CI/HI cs l sensitizing maximum at 485 m Example III S T J-CH=CHNH NHCH=CHC 1% N ci Hi I 508K 301K c=41i 1 It is an object of this invention to provide sensitizing maximum at 470-475 ml. new and useful sensitizing dyes for photographic silver halide emulsions. Example IV A further object is the provision of sensitizers showing slight coloring properties of the binding I agent of the photographic emulsion. s )LCILCH NH NH CH"CHTE Further objects will become apparent from 80:11 N the detailed specification following hereinafter. 40 I 6 It has been found that within this group such sensitizers possess especially valuable properties sensltlzmg maximum at 480 which are derived from aromatic diamines or tri- Example V amines containing in whatever position, i. e. in se cm the aromatic nucleus (or nuclei) or in the amino 45 B E a group (or amino groups) one or several carboxyl CH=CH"NH g H1 groups or sulfo acid groups. The most important N 00H N and progressive quality of these sensitizers is Q 6 h 11 ht olorin ro ert of the bindin t en 5 g c g p p y g sensitizing maximum at 495 mu.

agent of the photographic emulsion or of the paper support in the case of photographic papers. Furthermore the sensitizing intensity is very often increased by the introduction of these acid groups.

The dyestufls are incorporated into the emulsion itself in the usual manner or by bathing into the emulsion layer. The dyestuffs, naturally, may also be used in mixture with each other or Example VI sensitizing maximum at 490 m Example VII What I claim is: on, on, 1. A silver halide emulsion containing as a sensitizing dyestufl. therefor, compounds of the 1 g 1 following formula: H: CH=CH-NH NHCH=CH-C H;

0 ,Y.\ ,,Y\ coon c-on=cna-cn=cn6 C I CE: I -N% \N/ sensitizing maximum at 490-495 mu. 1/ R Example 10 in which A is an aromatic radicle containing at H;C-(fi-? s-( J-cn, least 1 benzene nucleus but not more than 2 benzene nuclei and being linked to each of the N C-CH-CHNH NHCH-OH-C n 9 adjacent CH- groups by a nitrogen atom, said OOH radicle containing at least 1 group selected from 02H; I 01115 I the class consisting of carboxyl and sulfonic acid sensitizing maximum at 515 m. groups, Y represents the atoms necessary to complete a heterocyclic ring system, B is alkyl Example IX and X is an anion. H=cs S--CH2 2. A silver halide emulsion containing a dye- O E stuff corresponding to the following formula:

N cntcoon H:CS Czh I 0 "000K 0,11, 1 mi //(IJCH=CHNH NHCH=OH(B\ 111, sensitizing maximum at 485 my. OOH

Example X I 1 3. A silver halide emulsion containing a dyei (7: stuff corresponding to the following formula:

-CH=CHNH NE-CH=CH- 30 H CH an H0 I I mc /(IJCH=OH-NH NHCH=OH(I3\ on, 00H 0 OH sensitizing maximum at 500 m 35 I Example XI 4. A silver halide emulsion containing a dyes om stuff corresponding to the following formula: mc s S CH2 H: (IJ-CH=CHNH NH-oracn-c H: f f' /JJ-CH=CH-NHQNHCH=CH E\ /N CH: CQHJ/ 1 cim \I coon sensitizing maximum at 480-485 m. I I

Example XII sensitizing maximum at 500 11111-- WAL'I'ER DIETERLE.

COOH 

